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CEO Assistant — AI Chief of Staff for Claude Code

Get instant, personalized business intelligence as a CEO — without switching dashboards or pasting spreadsheets.

The CEO Assistant is a free Claude Code skill that acts as a persistent AI Chief of Staff. It remembers your company, connects to your live tools, alerts you to business risks automatically, and adapts to your background — whether you're a technical founder, first-time CEO, or seasoned executive.

claude skills install https://github.com/Claudefarid/claude-ceo-skill

Covers 21 business domains · 20 live integrations · 25+ red flag alerts · Regional benchmarks · Adapts to CEO background


How to get an AI weekly business digest (automatically)

Most CEOs spend 2–3 hours on Monday morning pulling numbers from HubSpot, GA4, QuickBooks, and Slack to build a weekly summary. The CEO Assistant does this automatically.

Once connected to your tools, say:

give me my weekly business digest

You get a structured executive summary — revenue, pipeline, churn, marketing, and a prioritized action list — in under 60 seconds. Data is pulled live from connected tools. No copy-pasting.

Example output:

Acme Inc — Weekly Business Digest
Week ending June 21, 2026
Data: HubSpot ✅  GA4 ✅  QuickBooks ✅  Stripe ✅

🔴 ALERT — Pipeline Insufficient
Open pipeline ($380K) is below 2x your monthly target.
Action: Add 5 qualified opportunities before Friday.

Finance
MRR: $85,000 (+8% MoM) ✅ | Runway: 14 months ⚠️
Benchmark (Growth SaaS): Runway >18mo = safe. Start raise planning.

Sales
Closed: $42,000 | Pipeline: $380,000 ⚠️ | Win rate: 28% ✅

Marketing (live from GA4 + HubSpot)
Sessions: 12,400 (+15%) | Leads: 87 | CAC: $1,240 ✅

CEO Focus — Next 7 Days
1. Pipeline review call with sales team — Thursday
2. Call the 3 at-risk enterprise accounts personally
3. Approve Q3 content budget increase

How to use AI to understand your P&L report

CEOs receive P&L reports but often lack the context to know what the numbers mean for the business. Paste your P&L — the skill explains it in plain language, shows benchmarks, and tells you what to act on.

CEO: explain this month's P&L
[paste P&L]

Bottom line: Revenue grew 12% but net loss widened —
operating expenses scaled faster than revenue.

Revenue:       $85,000  (+12%) ✅
Gross Margin:  71%             ✅  Benchmark (Growth SaaS): >70% = excellent
Operating Exp: $94,000  (+28%) 🔴 Growing 16% faster than revenue
Net Loss:     ($33,650)        🔴

Action: Freeze non-essential hiring. Review top 3 expense
lines with CFO by end of week.

How to connect HubSpot to Claude Code

# Step 1 — Get your HubSpot access token
# Go to HubSpot → Settings → Integrations → Private Apps → Create

# Step 2 — Add the MCP server
claude mcp add hubspot \
  -e HUBSPOT_ACCESS_TOKEN=pat-YOUR-TOKEN \
  -- npx -y @hubspot/mcp-server

# Step 3 — Restart Claude Code and ask:
# "pull my HubSpot pipeline for this week"

The skill then pulls your pipeline, contacts, and deal stages automatically whenever you ask a sales question. Full guides for all 20 tools are in references/connect.md.


How to prep for a board meeting with AI

prep me for Thursday's board meeting

The skill pulls your latest metrics, builds a structured board update (highlights, lowlights, asks), identifies what questions board members are likely to ask based on your numbers, and prepares your answers.


How to get AI to monitor your business for problems

The CEO Assistant checks 25+ risk patterns every time you share data. Problems surface automatically — you don't have to ask.

What gets monitored:

Domain Alert triggers
Finance Runway < 6 months · Burn up >20% MoM · Margin below benchmark
Sales Pipeline < 2x target · Win rate < 20% · No deals in 30 days
Customer Success Churn > 3% · NRR < 90% · Key account at risk
HR Attrition > 25% · Critical role open 60+ days
Operations SLA < 90% · Critical bug open 48+ hours
Marketing CAC > LTV · ROAS < 1x · Leads declining 3+ months
M&A LOI exclusivity > 60 days · Revenue concentration risk

How to use AI for sales pipeline review

how is sales tracking this quarter?

With HubSpot or Salesforce connected, the skill pulls live pipeline data, compares it to your revenue target, calculates coverage ratio, identifies stalled deals, and tells you exactly where to focus.


How to find out which customers are at risk of churning

which customers are most at risk?

With Intercom or Zendesk connected, the skill identifies accounts showing churn signals — low engagement, unresolved tickets, usage drop — and prioritizes which ones the CEO should call personally.


Quick Start — first win in 3 steps

Step 1 — Install

claude skills install https://github.com/Claudefarid/claude-ceo-skill

Step 2 — Set up your company profile (2 minutes)

Open Claude Code and say:

set up my CEO assistant

The skill asks 9 questions and permanently saves your company context.

Step 3 — Get your first output immediately

After setup, say:

give me my weekly business digest

You get a structured executive summary with benchmarks and action items — using your actual company data.

Verify everything is working:

check skill health

Runs a full diagnostic. Shows which integrations are connected and what needs setup.


Install

One-command install

claude skills install https://github.com/Claudefarid/claude-ceo-skill

Manual install

cp -r ceo-assistant ~/.claude/skills/

Restart Claude Code. The skill activates on any business-related request.

Requirements: Claude Code (CLI or desktop) + Claude subscription. Integrations are optional — the skill works by pasting data too.


What is the CEO Assistant Claude skill?

The CEO Assistant is a Claude Code skill — a pre-built instruction set that gives Claude specialized expertise in business operations. Unlike generic AI chat, it:

  • Remembers your company — name, stage, metrics, goals, team, region stored in a local profile
  • Uses your real numbers — every answer references your actual data, not generic advice
  • Shows benchmarks — every metric compared to what good looks like for your stage and region
  • Alerts proactively — surfaces problems at the top of every response before you ask
  • Connects to your tools — pulls live data from HubSpot, Stripe, GA4, QuickBooks, and 16 more

Who is this for?

  • Technical founders — know the product, need help with finance, hiring, investor relations
  • First-time CEOs — want plain-language explanations of P&L, burn rate, board prep
  • Operators and career executives — want faster benchmarked business intelligence
  • Sales-background CEOs — want every answer framed around revenue impact
  • Any CEO running a startup, scaleup, or growth-stage company

Adapts to your background. Tell the skill once:

  • Technical → skips basics, goes deep on data and product
  • Sales → leads every answer with revenue impact
  • Finance/Operator → precise numbers, assumes metric fluency
  • First-time founder → explains concepts clearly on first use

20 live data integrations

Category Tools
Finance QuickBooks · Xero · Stripe
CRM & Sales HubSpot · Salesforce · Pipedrive
Marketing Google Analytics 4 · Google Ads · Mailchimp · ActiveCampaign
Product Analytics PostHog · Mixpanel
Customer Success Intercom · Zendesk
Productivity Google Sheets · Google Drive · Gmail · Notion · Slack
E-commerce Shopify

Step-by-step setup guide for every tool is built into the skill at references/connect.md.


21 business domains

Finance · Sales · Marketing · Customer Success · HR · Operations · Product · Investor Relations · Meetings · Communications · Strategy & OKRs · Legal · PR · Hiring · Competitive Intelligence · Weekly Digest · M&A · Exit Planning · International Expansion · Dashboard & KPIs · Report Summarization


CEO Assistant vs alternatives

CEO Assistant Generic ChatGPT Hiring a COO Manual dashboards
Remembers your company
Pulls live data ✅ 20 tools Varies
Proactive alerts ✅ 25+ triggers
Industry benchmarks ✅ Global + regional Varies
Setup time 2 minutes Instant 3–6 months Weeks
Cost Free $20/mo $150K+/yr Tool costs
Available 24/7

Frequently Asked Questions

What is a Claude Code skill?

A Claude Code skill is a pre-built instruction set that gives Claude specialized expertise in a domain. Skills install locally and activate automatically when you ask a relevant question. The CEO Assistant skill turns Claude into a persistent AI Chief of Staff with memory of your company.

Does the CEO Assistant skill work without tool integrations?

Yes. You can paste reports directly and the skill will analyze them, extract key metrics, show benchmarks, and flag risks. Integrations automate the data collection so you don't have to paste manually.

How does the CEO Assistant remember my company across sessions?

During setup, the skill asks 9 questions and saves your answers to a local company-profile.md file. This file is loaded at the start of every conversation. You can update it anytime by saying "update my company profile" or by sharing a new report — the skill extracts and saves updated numbers automatically.

Which CEO backgrounds does the skill support?

Technical/Engineering, Sales/Commercial, Finance/Operator, First-time founder, and General executive. The skill adjusts its explanation depth based on your background — a technical CEO gets deep data analysis with no hand-holding; a first-time founder gets clear explanations of every term.

What regions and industries are benchmarks available for?

Benchmarks cover: North America (SaaS, services, ecommerce, marketplace), South Asia (Bangladesh, India, Pakistan — SaaS, IT services, BPO), Southeast Asia, Middle East (UAE, Saudi Arabia), and UK & Europe. Industry types: SaaS, tech services, ecommerce, marketplace, BPO.

How long does it take to set up integrations?

HubSpot and Google Analytics 4: under 10 minutes. Stripe: under 10 minutes. QuickBooks, Salesforce: 15–20 minutes. All integrations have step-by-step setup guides built into the skill — say "connect my HubSpot" and the skill walks you through it.

Is my business data stored anywhere external?

No. The skill runs locally in Claude Code. Your company profile is stored in a file on your own machine. Data pulled from integrations is processed within your Claude session and not stored by Anthropic or any third party beyond your existing tool providers.

Can I use the CEO Assistant skill for my whole leadership team?

Yes. Any member of the leadership team can install and use the skill independently. Each user maintains their own local company profile. There is no shared account or team workspace required.

How is this different from just asking ChatGPT or Claude directly?

Generic AI gives generic answers. The CEO Assistant knows your company name, your actual MRR, your runway, your goals, your team, and your region. It also compares your metrics to industry benchmarks and proactively flags risks — things a generic AI prompt cannot do without context you'd have to re-paste every time.

What happens if I don't have any integrations connected?

The skill asks you to paste the relevant data (a report, a spreadsheet, a summary). It then analyzes it, updates your company profile automatically, and gives you the same quality of insight. Integrations save time but are not required.


Skill structure

claude-ceo-skill/
├── SKILL.md                     ← Routing, red flags, output rules
├── company-profile.md           ← Your company context (local, auto-maintained)
├── llms.txt                     ← AI crawler index for search engine citability
├── README.md
└── references/
    ├── connect.md               ← Integration setup wizard (20 tools)
    ├── prompts.md               ← 60+ example prompts by domain
    ├── integrations.md          ← Live data pull logic
    ├── setup.md                 ← Company onboarding + memory rules
    ├── benchmarks.md            ← Global + regional benchmarks
    ├── finance.md               ← P&L, cash, burn, runway
    ├── sales.md                 ← Pipeline, quota, win/loss
    ├── marketing.md             ← CAC, LTV, channels, ROAS
    ├── dashboard.md             ← KPI reviews, business reviews
    ├── operations.md            ← SLAs, vendors, incidents
    ├── hr.md                    ← Team, attrition, org changes
    ├── product.md               ← Roadmap, bugs, releases
    ├── customer-success.md      ← Churn, NPS, at-risk accounts
    ├── investor.md              ← Board prep, fundraising
    ├── meetings.md              ← Agendas, action items
    ├── communications.md        ← All-hands, crisis, announcements
    ├── strategy.md              ← OKRs, quarterly planning
    ├── legal.md                 ← Contracts, compliance, IP
    ├── pr.md                    ← Crisis, press releases
    ├── hiring.md                ← Job descriptions, interviews, comp
    ├── competitive.md           ← Competitor profiles, battle cards
    ├── weekly-digest.md         ← Full business digest format
    ├── ma.md                    ← M&A, exit planning, valuation
    ├── international.md         ← Market entry, EOR, compliance
    └── summarize.md             ← General report summarization

License

MIT — free to use, fork, and distribute.


Built by

Farid Swadhin — AI tools for founders and operators.

If this skill saves you time, connect on LinkedIn or star the repo — it helps others find it.


The AI Chief of Staff that knows your business — not just your question.

About

Claude AI Skills for CEO or Chief of Staff. 21 business domains, 20 live integrations (HubSpot, GA4, Stripe, Notion, Slack & more), 25+ red flag alerts, regional benchmarks. Adapts to your background. Install in Claude Code.

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